Photochemical Synthesis of 1,4-Dicarbonyl Bifluorene Compounds via Oxidative Radical Coupling Using TEMPO as the Oxygen Atom Donor

Jincheng Xu; Aishun Ding; Yanbin Zhang; Hao Guo

doi:10.1021/acs.joc.0c02781

Photochemical Synthesis of 1,4-Dicarbonyl Bifluorene Compounds via Oxidative Radical Coupling Using TEMPO as the Oxygen Atom Donor

J Org Chem. 2021 Feb 19;86(4):3656-3666. doi: 10.1021/acs.joc.0c02781. Epub 2021 Jan 29.

Authors

Jincheng Xu¹, Aishun Ding¹, Yanbin Zhang¹, Hao Guo¹

Affiliation

¹ Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, People's Republic of China.

PMID: 33513019
DOI: 10.1021/acs.joc.0c02781

Abstract

A visible-light-induced metal-free synthesis of 1,4-dicarbonyl compounds from alkyne-containing aryl iodides via photochemical C-I bond cleavage, intramolecular cyclization, oxidation, and intermolecular radical coupling sequence is reported. TEMPO was employed as the oxygen atom donor in this transformation. This protocol provided a new strategy for the synthesis of 1,4-dicarbonyl bifluorene compounds.